Production of certain imidazopyridinyl-methyl-benzene sulfonamides

Abstract

Compounds of general formula I; <IMAGE> I wherein: A1 is =N-, =CH- or =CR1-; A2 is =N-, =CH- or =CR2-; provided that, when one of A1 and A2 is a nitrogen atom, the other of A1 and A2 is other than a nitrogen atom; wherein the rest of the variables are defined in the specification; and their pharmaceutically and veterinarily acceptable acid addition salts and hydrates are antagonists of platelet activating factor (PAF) and as such are useful in the treatment or amelioration of various diseases or disorders mediated by PAF.

We claim: 
     
       1. A process for preparing a compound of general formula I ##STR81## wherein: A 1  is ═N--, ═CH-- or ═CR 1  --; A 2  is ═N--, ═CH-- or ═CR 2  --; provided that one of A 1  and A 2  is a nitrogen atom and the other of A 1  and A 2  is other than a nitrogen atom;     R represents hydrogen, --C 1  --C 6  alkyl, --C 2  --C 6  alkenyl, --C 2  --C 6  alkynyl, halogen or OC 1  --C 6  alkyl;   R 1  and R 2  each independently represents hydrogen, --C 1  --C 6  alkyl, --C 2  --C 6  alkenyl, --C 2  --C 6  alkynyl, halogen, --CN, --CO 2  H, --CO 2  C 1  --C 6  alkyl, --COHN 2  --CHO, --CH 2  OH, --CF 3  --OC 1  --C 6  alkyl, --SC 1  --C 6  alkyl, --SOC 1  --C 6  alkyl, --SO 2  C 1  --C 6  alkyl, --NH 2  --NHCOMe or --NO 2  or R 1  R 2  together with the carbon atoms to which they are attached form a fused phenyl ring;   R 3  represents hydrogen, --C 1  --C 6  alkyl, --C 2  --C 6  alkenyl, --C 2  --C 6  alkynyl, --OC 1  --C 6  alkyl, --SC 1  --C 6  alkyl, --(C 1  --C 6  alkyl)OC 1  --C 6  alkyl, --(C 1  --C 6  alkyl)SC 1  --C 6  alkyl, --CF 3  --(C 1  --C 6  alkyl)phenyl, --C 3  --C 8  cycloalkyl, --C 4  --C 8  cycloalkenyl, --(C 1  --C 6  alkyl)C 3  --C 8  cycloalkyl, --(C 1  --C 6  alkyl)C 4  --C 8  cycloalkenyl or thiophenyl;   R 4  represents hydrogen, --C 1  --C 6  alkyl, --C 2  --C 6  alkenyl, --C 2  --C 6  alkynyl, --CO 2  C 1  --C 6  alkyl, --SC 1  --C 6  alkyl, --(C 1  --C 6  alkyl)SC 1  --C 6  alkyl, --(C 1  --C 6  alkyl)OC 1  --C 6  alkyl, --(C 1  --C 6  alkyl)phenyl or thiophenyl;   R 5  represents hydrogen, --C 1  --C 6  alkyl, --C 2  --C 6  alkenyl, --C 2  --C 6  alkynyl, --COC 1  --C 6  alkyl, --CO 2  C 1  --C 6  alkyl, --(CO 2  C 1  --C 6  alkyl)phenyl, --(C 1  --C 6  alkyl)CO 2  C 1  --C 6  alkyl, --(C 1  --C 6  alkyl)phenyl, --C 3  --C 8   cycloalkyl, C 4  --C 8  cycloalkenyl or phenyl optionally substituted by one or more substituents selected from --C 1  --C 6  alkyl, --OC 1  --C 6  alkyl, halogen, --CF 3  --CN;   m is an integer from 0 to 3;   z is either a --CR 6  R 7  R 8  or --CR 6  ═CR 7  R 8  group;   wherein each of R 6  R 7 , and R 8  independently represents hydrogen, halogen, --C 1  --C 18  alkyl optionally substituted by one or more halogen atoms, --C 2  --C 18  alkenyl, --C 2  --C 18  alkynyl, --(C 1  --C 6  alkyl)OC 1  --C 18  alkyl, --(C 1  --C 6  alkyl)SC 1  --C 18  alkyl, --(C 1  --C 6  alkyl)O(C 1  --C 6  alkyl)OC 1  --C 6  alkyl, --(C 1  --C 6  alkyl)S(C 1  --C 6  alkyl)OC 1  --C 6  alkyl, --(C 1  --C 6  alkyl)O(C 1  --C 6  alkyl)SC 1  --C 6  alkyl, --(C 1  --C 6  alkyl)S(C 1  --C 6  alkyl)SC 1  --C 6  alkyl), --C 1  --C 6  alkyl)OC 2  --C 6  alkenyl, --C 3  --C 8  cycloalkyl, --C 4  --C 8  cycloalkenyl, --(C 1  --C 6  alkyl)C 3  --C 8   cycloalkyl, --(C 1  --C 6  alkyl)C 4  --C 8  cycloalkenyl, --(C 1  --C 6  alkyl)OC 3  --C 8  cycloalkyl, --(C 1  --C 6  alkyl)OC 4  --C 8  cycloalkenyl, --(C 1  --C 6  alkyl)SC 3  --C 8  cycloalkyl, --(C 1  --C 6  alkyl)SC 4  --C 8  cycloalkenyl, --(C 1  --C 6  alkyl)N(C 1  --C 6  alkyl) 2  --(C 1  --C 6  alkyl)morpholino, --(C 1  --C 6  alkyl)OCH 2  Ph, --CH 2  OSi(C 1  --C 6  alkyl) 3  --CH 2  OSiPh 2  C 1  --C 6  alkyl or a group --D wherein D represents a group; ##STR82## wherein n is an integer from 0 to 3and each of R 9  R 10  and R 11  is independently hydrogen, --C 1  --C 6  alkyl, --OC 1  --C 6  alkyl, --SC 1  --C 6  alkyl, --N(C 1  --C 6  alkyl) 2  --C 2  --C 6  alkenyl, --C 2  --C 6  alkynyl, --OCH 2  Ph, halogen, --CN, --CF 3  --CO 2  H, --CO 2  C 1  --C 6  alkyl, --CONH 2  --CONHC 1  --C 6  alkyl, --CONH(C 1  --C 6  alkyl) 2  --CHO, --CH 2  OH, --NH 2  --NHCOC 1  --C 6  alkyl, --SOC 1  --C 6  alkyl, or --SO 2  C 1  --C 6  alkyl;    or a pharmaceutically or veterinarily acceptable acid addition salt or hydrate thereof;    the process comprising:   treating a substituted diamino compound of general formula IV ##STR83##  wherein A 1  A 2  R, R 1  R 2  R 4  R 5  m and z are as defined in general formula I, with a carboxylic acid of general formula V   R.sup.3 CO.sub.2 H                                         V        wherein R 3  is as defined in general formula I.